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Quite a few books told you that writing tests upfront is a good thing. They're right, but unfortunately you normally also need some documentation about how to use the well tested service/applicaton.
Using "cucumber" makes both possible and "easy": Writing tests upfront, but also generating documentation from those tests. Accompanied with "aruba", you can use it to generate documentation from your tests for commandline applications. This is what cucumber and rspec do for their documentation.
This talk focuses on testing commandline applications and having documentation for those. It starts with thoughts about documentation itself and then gets into problems you might face if you try to convince administrators to document their scripts. It closes with a solution for that task.
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Living Documentation for commandline applications - A contract between you and your users
Dennis Günnewig is a system administrator responsible for a lot of HTTP proxy servers in large customer environments. To make his daily job a little bit easier he writes quite a few scripts and commandline applications. For those scripts and applications which are more complex he uses "cucumber" and "aruba" to write and run a test suite. Besides that he's one of the maintainers of "aruba" and loves to write ruby code.